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Azithromycin information


Azithromycin
Clinical data
Trade namesZithromax, others[1]
Other names9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A
AHFS/Drugs.comMonograph
MedlinePlusa697037
License data
  • US DailyMed: Azithromycin
Pregnancy
category
  • AU: B1[2]
Routes of
administration
By mouth, intravenous, eye drops
Drug classMacrolide antibiotic
ATC code
  • J01FA10 (WHO) S01AA26 (WHO) J01RA07 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[4]
  • CA: ℞-only[5][6]
  • UK: POM (Prescription only)[7]
  • US: WARNING[3]Rx-only[8]
  • EU: Rx-only[9]
Pharmacokinetic data
Bioavailability38% for 250 mg capsules
MetabolismLiver
Elimination half-life68 h
ExcretionBile duct[8]
Identifiers
IUPAC name
  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
CAS Number
  • 83905-01-5 checkY
PubChem CID
  • 55185
IUPHAR/BPS
  • 6510
DrugBank
  • DB00207 checkY
ChemSpider
  • 10482163 checkY
UNII
  • J2KLZ20U1M
KEGG
  • D07486 checkY
ChEBI
  • CHEBI:2955 checkY
ChEMBL
  • ChEMBL529 checkY
NIAID ChemDB
  • 007311
CompTox Dashboard (EPA)
  • DTXSID8030760 Edit this at Wikidata
ECHA InfoCard100.126.551 Edit this at Wikidata
Chemical and physical data
FormulaC38H72N2O12
Molar mass748.996 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]2(C)O)[C@@H]3O
InChI
  • InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1 checkY
  • Key:MQTOSJVFKKJCRP-BICOPXKESA-N checkY
  (verify)

Azithromycin, sold under the brand names Zithromax (in oral form) and Azasite (as an eye drop), is an antibiotic medication used for the treatment of a number of bacterial infections.[10] This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections.[10] Along with other medications, it may also be used for malaria.[10] It is administered by mouth, into a vein, or into the eye.[10]

Common side effects include nausea, vomiting, diarrhea and upset stomach.[10] An allergic reaction, such as anaphylaxis, or a type of diarrhea caused by Clostridium difficile is possible.[10] Azithromycin causes QT prolongation that may cause life-threatning arrythmias such as torsades de pointes.[11] No harm has been found with its use during pregnancy.[10] Its safety during breastfeeding is not confirmed, but it is likely safe.[12] Azithromycin is an azalide, a type of macrolide antibiotic.[10] It works by decreasing the production of protein, thereby stopping bacterial growth.[10][13]

Azithromycin was discovered in Croatia in 1980 by the pharmaceutical company Pliva and approved for medical use in 1988.[14][15] It is on the World Health Organization's List of Essential Medicines.[16] The World Health Organization lists it as an example under "Macrolides and ketolides" in its Critically Important Antimicrobials for Human Medicine (designed to help manage antimicrobial resistance).[17] It is available as a generic medication[18] and is sold under many brand names worldwide.[1] In 2021, it was the 97th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[19][20]

  1. ^ a b "Azithromycin International Brands". Drugs.com. Archived from the original on 28 February 2017. Retrieved 27 February 2017.
  2. ^ "Azithromycin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 18 June 2020. Retrieved 24 December 2019.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Zithromax azithromycin 500mg (as dihydrate) tablet blister pack (58797)". Therapeutic Goods Administration (TGA). 12 August 2022. Retrieved 26 April 2024.
  5. ^ "Zithromax Product information". Health Canada. 16 January 2013. Retrieved 26 April 2024.
  6. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
  7. ^ "Zithromax Summary of Product Characteristics (SmPC)". (emc). 5 February 2024. Retrieved 26 April 2024.
  8. ^ a b Cite error: The named reference Zithromax FDA label was invoked but never defined (see the help page).
  9. ^ "List of nationally authorised medicinal products Active substance: azithromycin (systemic use formulations)" (PDF). European Medicine Agency. 14 January 2021. Archived (PDF) from the original on 18 August 2021. Retrieved 10 March 2023.
  10. ^ a b c d e f g h i "Azithromycin". The American Society of Health-System Pharmacists. Archived from the original on 5 September 2015. Retrieved 1 August 2015.
  11. ^ Dunker A, Kolanczyk DM, Maendel CM, Patel AR, Pettit NN (November 2016). "Impact of the FDA Warning for Azithromycin and Risk for QT Prolongation on Utilization at an Academic Medical Center". Hosp Pharm. 51 (10): 830–833. doi:10.1310/hpj5110-830. PMC 5135431. PMID 27928188.
  12. ^ "Azithromycin use while Breastfeeding". Archived from the original on 5 September 2015. Retrieved 4 September 2015.
  13. ^ "Azithromycin Stops The Growth of Bacteria" (in German). Archived from the original on 12 May 2020. Retrieved 24 December 2017.
  14. ^ Greenwood D (2008). Antimicrobial drugs : chronicle of a twentieth century medical triumph (1st ed.). Oxford: Oxford University Press. p. 239. ISBN 978-0-19-953484-5. Archived from the original on 5 March 2016.
  15. ^ Alapi EM, Fischer J (2006). "Table of Selected Analogue Classes". In Fischer J, Ganellin CR (eds.). Analogue-based Drug Discovery. Weinheim: Wiley-Vch Verlag GmbH & Co. KGaA. p. 498. ISBN 978-3-527-31257-3. Archived from the original on 14 January 2023. Retrieved 2 April 2020.
  16. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  17. ^ World Health Organization (2018). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 978-92-4-151552-8. License: CC BY-NC-SA 3.0 IGO.
  18. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. ISBN 978-1-284-05756-0.
  19. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  20. ^ "Azithromycin - Drug Usage Statistics". ClinCalc. Archived from the original on 18 January 2024. Retrieved 14 January 2024.

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penicillin-resistant illnesses. Later macrolides developed, including azithromycin and clarithromycin, stemmed from chemically modifying erythromycin; these...

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with other measures. Treatment options include oral azithromycin and topical tetracycline. Azithromycin is preferred because it can be used as a single oral...

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decreases spread. Treatment is typically with antibiotics, including azithromycin by mouth or benzathine penicillin by injection. Without treatment, physical...

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Chlamydia

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cured by antibiotics with typically either azithromycin or doxycycline being used. Erythromycin or azithromycin is recommended in babies and during pregnancy...

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Vladimir Zelenko

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promoting a three-drug combination of hydroxychloroquine, zinc sulfate, and azithromycin as part of an experimental outpatient treatment for COVID-19 that he...

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Urethritis

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injection dose of ceftriaxone 250 mg intramuscularly and oral dose of azithromycin 1g simultaneously. Cefixime 400 mg oral single dose can be used as an...

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Whooping cough

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within six weeks of symptom onset. Antibiotics used include erythromycin, azithromycin, clarithromycin, or trimethoprim/sulfamethoxazole. Evidence to support...

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Gonorrhea

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not having sex. Treatment is usually with ceftriaxone by injection and azithromycin by mouth. Resistance has developed to many previously used antibiotics...

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Pliva

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Radobolja-Lazarevski and Zrinka Tamburašev [sh] led by Dr. Slobodan Đokić, discovered azithromycin in 1980.[citation needed] In June 2002, the company acquired Sidmak for...

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treatment with azithromycin on asthma exacerbations and quality-of-life in patients with severe, refractory asthma have resulted in azithromycin now being...

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antibiotic: Ciprofloxacin, Doxycycline, Minocycline, Tetracycline, Imipenem, Azithromycin Extended-spectrum antibiotic: Ampicillin Narrow-spectrum antibiotic:...

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pregnancy. The concurrent use of hydroxychloroquine and the antibiotic azithromycin appears to increase the risk for certain serious side effects with short-term...

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with cytochrome P-450A (CYP) 3A4: an update focused on clarithromycin, azithromycin and dirithromycin". British Journal of Clinical Pharmacology. 50 (4):...

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ibuprofen, or if bacterial in origin, antibiotics, e.g. amoxicillin and azithromycin. Surgical removal (tonsillectomy) may be advised if the tonsils obstruct...

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prepare food for others. Typhoid is treated with antibiotics such as azithromycin, fluoroquinolones, or third-generation cephalosporins. Resistance to...

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have been reported in northern Thailand. Rifampicin and azithromycin are alternatives. Azithromycin is an alternative in children and pregnant women with...

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Atovaquone

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been observed. For babesia, it is often used in conjunction with oral azithromycin. Trimethoprim/sulfamethoxazole (TMP-SMX, Bactrim) is generally considered...

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such as oral rehydration solution is important. Antibiotics such as azithromycin may be used to treat cases associated with travelling in the developing...

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success rate. Azithromycin and doxycycline have equal efficacy to treat C. trachomatis with 97 and 98 percent success, respectively. Azithromycin is dosed...

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as cephazolin plus a macrolide such as azithromycin is recommended. A fluoroquinolone may replace azithromycin but is less preferred. Antibiotics by mouth...

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